Samantha and Matthew Orley's Wedding in Aspen

Eight and a half years later, the couple got engaged. "The proposal was really simple and sweet," says Samantha. "We had a work event that night and got home late. Matt had actually picked a fight with me earlier that evening, and I kind of stormed into the apartment and was surprised to find he had filled the place with flowers earlier in the day. He got down on both knees, and I was completely shocked. The next morning we flew to the Dominican Republic where my grandparents live to spend the weekend with them. They are in their 90s (and just celebrated their 66th anniversary!), and it was really special to be able to share that moment with them."

Samantha and Matt always knew they wanted to get married outdoors. "We've been together for a long time, so our family and friends are really intertwined," explains Samantha. "As a result, we loved the idea of a destination wedding where everyone could spend time together for an entire weekend. Aspen has become such a special place to us, and it was important to us that the wedding embrace as much of the natural beauty of the surrounding area as possible."

As for the dress: "I was looking for something that felt true to my style, and so I had a pretty specific idea of what I wanted to wear--the hardest part was finding it! I ended up working with New York designer Elizabeth Fillmore to create something completely custom." Meanwhile, Matthew opted for a suit of his own design with the bride's name embroidered on the cuff of his left sleeve.

On the big day, the bride and groom were determined to have the ceremony outdoors despite the touch-and-go weather. "We weren’t sure if we were going to get through it and stay dry, but as soon as there was a break in the skies, we started the music and just went for it," says Samantha. "As we walked down the aisle, there were whistles and cheers from the rowdy crowd."

The couple's grandparents, parents, and siblings proceeded down the aisle to the original versions of Nina Simone’s “To Love Somebody” and Otis Redding’s "That’s How Strong My Love Is," while Samantha walked to **Aretha Franklin’**s “You’re All I Need to Get By," a personal favorite of hers.

The couple stood under a simple chuppah of Aspen trees together with their parents and had their siblings at their sides. "Although it was a little cold and a little rainy—the ceremony was punctuated by the popping sounds of umbrellas opening and closing—our guests stayed in great spirits," says Samantha. "It ended up being beautiful with the incredible view of the gray clouds against the mountains."

After the ceremony, they kicked off the reception with their first dance (Sam Cooke’s "It’s All Right / For Sentimental Reasons”) and the dancing didn’t stop after that. Guests enjoyed a family-style dinner that was served while Matt's brothers, Alex Orley and Jason Orley, gave their speeches. After dinner, the band, Fifty Amp Fuse, a Detroit-based cover band, really brought the house down. "We’re fairly certain that every one of our guests was on stage at the mic at some point in the evening," says Samantha. "At one point, I was carried across the dance floor standing atop of a drinks platter and that has come to sum up the entire night.